You'd think life would be pretty good for Ben Stiller. In the last six years, he's been part of six movies that made more than $100 million. Another one, the indie drama Greenberg, earned him great reviews. He's one of the biggest comic stars in the world. A lot of people would love to be in his position, even if The Watch does look pretty bad.

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But last month's Tad Friend profile in The New Yorker painted a picture of Stiller as anything but content—instead, he comes across as a driven, deeply insecure control freak who's still beating himself up because Paul Thomas Anderson didn't put him in Punch-Drunk Love. You get the sense that Stiller is constantly concerned that he's popular but not respected, that as much as he'd like to be known as the edgy auteur of Permanent Midnight, most everybody just thinks of him as the Focker dude.

The guy who made The Ben Stiller Show 20 years ago would have found this all hilarious. That guy wishes he had such problems.

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Premiering in September 1992 and airing on Sunday nights on Fox, The Ben Stiller Show was the then-little-known Stiller's second show. (He'd done a short-lived variety program on MTV a couple years earlier.) The early '90s was a fertile time for sketch comedy. There was Saturday Night Live, of course, but there were also In Living Color and The Kids in the Hall, which were both looked at as cooler, fresher versions of SNL. The Ben Stiller Show came on opposite 60 Minutes and got colossally abysmal ratings, lasting all of 12 episodes. (The program's poor showing was so self-evident that guest star Dennis Miller appeared in the 10th episode to tell Stiller he shouldn't take it too badly—everybody gets axed eventually.) But because the show received great reviews, won an Emmy for writing, and was an early proving ground for everybody from co-creator Judd Apatow to cast member Andy Dick, The Ben Stiller Show is generally remembered as an undiscovered gem, this little slice of pure, uncut, brilliant Stiller that audiences were too dumb to get at the time.

When you go back and watch the show now, though, you see that's not exactly the case. While it can be pretty funny, The Ben Stiller Show is a mess, Stiller and his cohorts trying a little bit of everything to see if it'll work. The format was pretty simple: Stiller hosted each episode, usually accompanied by a guest (Flea, Star Trek's James Doohan, an impossibly young Sarah Jessica Parker), and then he'd cut to short filmed bits starring him and and his cast (Dick, Janeane Garofalo, Bob Odenkirk), which were usually send-ups of movies or bands that were popular at the time. (Pearl Jam jokes!) Soon, a recurring theme started to solidify: His guests pretended to be unhappy that they were there, and Stiller played the insecure dweeb in the interview segments, as if he too knew that he had no right having his own show. He wasn't some cocky up-and-comer; he was a self-effacing guy whose expression was stuck in an I'm-so-sorry rictus.

But despite its hit-or-miss quality, what's really great about revisiting The Ben Stiller Show is that you get to see a Stiller who seems free of the burdens that Friend describes in the New Yorker piece. He may not be successful—and he may have been a control freak then, too—but he sure seems like he's having a lot of dopey fun. Although Entertainment Weekly's Ken Tucker glowingly described the show's parodies at the time as "exhilaratingly meanspirited," Stiller's impersonations—of Bruce Springsteen, Tom Cruise, Bono, Metallica's James Hetfield, and others—now actually feel pretty harmless. Maybe that's because it's been 20 years, but it's also because Stiller's satire has always lacked a cruel streak. As Stiller explains in the show's DVD commentary, he only parodied things that he deep down really loved. That comes through in the sketches. (For instance, there are a lot of vicious ways to ridicule Bono, especially at the height of U2's Achtung Baby popularity. Bar mitzvah gags and fake Zoo TV talk shows are not two of them.) Although Stiller has shown an edge in movies like Flirting With Disaster and Greenberg, you wonder if he's just always meant to be the lovable schlub—the slow-burning, put-upon loser who eventually blows up at Robert De Niro when he's had enough. (By comparison, Dick's takedown of Sandra Bernhard and Garofalo's frighteningly accurate Tabitha Soren impression still have a mean streak to them. Those two actors projected a contempt for others that Stiller never summoned—maybe that's why they were never big stars.)

But even if Ben Stiller is lovably ragged, Stiller's ambitions are evident. He directed a lot of the sketches, and they're shot on film with no laugh track added afterward. That was pretty nervy for the time. (While Kids in the Hall incorporated filmed segments, there was still a live studio audience for other sketches.) Like The Larry Sanders Show, which started out a month earlier, The Ben Stiller Show felt sophisticated simply because there wasn't any laughter, as if they expected that you could figure out what was funny without having someone cue you. Plus, Stiller's visual eye was pretty sharp: Just look at his dead-on send-up of Husbands and Wives, redone with horror characters like Frankenstein's monster, or his black & white Lassie spoof that substituted Charles Manson for the loyal collie. The recreations rewarded you for being smart enough not only to get the references but to appreciate the care that went into their look. But these parodies don't feel like fiery broadsides at Hollywood—they're more like savvy calling cards from a guy who grew up with showbiz parents (comedians Jerry Stiller and Anne Meara) and is spoiling for his chance.

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What's funny is that Stiller, though the show bears his name, doesn't stand out as the biggest talent among his castmates and writers. They were all practically nobodies at the time. Apatow had only done some Tom Arnold specials. Dick and Garofalo hadn't been in anything to speak of. Odenkirk was probably the most famous, thanks to his time as a writer on Saturday Night Live. (His great Ben Stiller-esque Mr. Show was waiting in the wings.) But even among this bunch, Stiller seems blandly anonymous. Dick was the weird, flamboyant one. Garofalo was the sullen, sarcastic one. Odenkirk was the cerebral craftsman. And Stiller? He did a funny Cruise and a funny Springsteen, but otherwise he was the charming, handsome, somewhat ordinary guy at the center. Twenty years later, he's still that guy—just way more famous.

In the New Yorker profile, he longs to be more than just that guy, but after watching The Ben Stiller Show, I'm not sure he can be—it's in his DNA to be likeable and appealing, even when he's trying to be satirical. (Tropic Thunder is more goofy than it is blistering.) Maybe the Ben Stiller of 20 years ago would have goofed on Night at the Museum or The Watch, but he would've done it gently, sweetly. He's not just the nice guy—he proved that with Greenberg and parts of The Cable Guy—but as The Ben Stiller Show demonstrates, nice is his bread-and-butter. Nice is what got him here in the first place.

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Grierson & Leitch is a regular column about the movies. Follow us on Twitter, @griersonleitch.